After years of trying every padded crotch out there I have reached the same conclusion as a few others here. Padded crotches just squish into my girly bits (makes me feel like I'm in 7th grade to say that) and cause chafing, boils and swelling. Angelina Jolie ring a bell? I certainly agree that it is counter-productive to put a padded crotch over a saddle cut-out that is designed to give your soft tissues somewhere to go. When I first realized this, I cut out the center of all my pads. That caused some serious problems and I do not recommend it at all. Fail! Then, a few months later I started spinning. After a month of spinning with plain compression shorts, I wore padded shorts one morning. Immediate problems. I literally split open the skin on my labia and dealt with the accompanying boil for weeks. The lights came on.

Now I ride without a pad at all and have a much more comfortable ride. I have invested in some very expensive seats that serve me well- a Selle Italia Diva and a Terry ti. Generous cut-out without pressure ridges on each and the padded nose on the Diva for time trials. I do wish I could find padding just for my sit-bones. But I'll live with this over the alternatives. I do think that it may take some conditioning to get comfortable like this but no amount of conditioning ever got me comfortable with a padded crotch.

Ultimately, all you can do is ride and find out. Before you invest a lot of money, perhaps you have friends that aren't squeamish about these things that would loan you some to try. I have a stack of padded shorts you could have.